GB829601A - Improvements in or relating to the polymerisation of methacrolein - Google Patents
Improvements in or relating to the polymerisation of methacroleinInfo
- Publication number
- GB829601A GB829601A GB28440/57A GB2844057A GB829601A GB 829601 A GB829601 A GB 829601A GB 28440/57 A GB28440/57 A GB 28440/57A GB 2844057 A GB2844057 A GB 2844057A GB 829601 A GB829601 A GB 829601A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methacrolein
- soluble
- catalyst
- polymethacrolein
- finely
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 239000005955 Ferric phosphate Substances 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 abstract 2
- 230000000274 adsorptive effect Effects 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 abstract 2
- 229940032958 ferric phosphate Drugs 0.000 abstract 2
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 abstract 2
- 229910000399 iron(III) phosphate Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 239000004342 Benzoyl peroxide Substances 0.000 abstract 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 abstract 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N CuO Inorganic materials [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 abstract 1
- 239000004159 Potassium persulphate Substances 0.000 abstract 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 235000019400 benzoyl peroxide Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000010941 cobalt Substances 0.000 abstract 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 abstract 1
- 229910000428 cobalt oxide Inorganic materials 0.000 abstract 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000004815 dispersion polymer Substances 0.000 abstract 1
- 239000011953 free-radical catalyst Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 235000014413 iron hydroxide Nutrition 0.000 abstract 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 abstract 1
- 229910000480 nickel oxide Inorganic materials 0.000 abstract 1
- 229910000484 niobium oxide Inorganic materials 0.000 abstract 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 abstract 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 abstract 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 abstract 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 abstract 1
- 235000019394 potassium persulphate Nutrition 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- -1 sulphoxalate Chemical compound 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/14—Polymerisation of single aldehydes not provided for in groups C08G2/08 - C08G2/12
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02B—INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL
- F02B33/00—Engines characterised by provision of pumps for charging or scavenging
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02M—SUPPLYING COMBUSTION ENGINES IN GENERAL WITH COMBUSTIBLE MIXTURES OR CONSTITUENTS THEREOF
- F02M2700/00—Supplying, feeding or preparing air, fuel, fuel air mixtures or auxiliary fluids for a combustion engine; Use of exhaust gas; Compressors for piston engines
- F02M2700/33—Compressors for piston combustion engines
- F02M2700/331—Charging and scavenging compressors
- F02M2700/335—Control therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Abstract
Methacrolein is polymerized by contacting it in a polar solvent medium with less than 0.02 mol. per cent of the monomer of a free radical catalyst in the presence of a finely-divided adsorptive surface at a temperature below 50 DEG C., and recovering a dispersion of a high molecular weight soluble polymethacrolein having an inherent viscosity in dimethyl formamide of 0.3 to 3.0, the polar p solvent medium being one in which the methacrolein is soluble but the polymethacrolein is not. The solvent is preferably a mixture of water and methanol and the catalyst is preferably a redox system such as hydrogen peroxide with thiourea, benzoyl peroxide with dimethyl-p-toluidine or potassium persulphate, soluble ferric phosphate, cupric, cuprous, nickel, cobalt or niobium oxide or vanadium pentoxide in combination with one or more of sodium bisulphite, thiosulphate, sulphoxalate, hypophosphite or phosphite. The adsorptive surface may be a finely-divided silica surface formed in situ in the reaction zone such as by hydrolysis of tetraethyl orthosilicate, or may be alumina, titania or zirconia or insoluble iron hydroxide formed when ferric phosphate is one of the catalyst ingredients. The polymer dispersion may be stabilized by addition to the polymerization mixture of a surface-active agent such as ammonium perfluorocaprylate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US612926A US2993878A (en) | 1956-10-01 | 1956-10-01 | Polymerization of methacrolein |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB829601A true GB829601A (en) | 1960-03-02 |
Family
ID=24455160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB28440/57A Expired GB829601A (en) | 1956-10-01 | 1957-09-09 | Improvements in or relating to the polymerisation of methacrolein |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US2993878A (en) |
| BE (1) | BE561137A (en) |
| CH (1) | CH371596A (en) |
| DE (1) | DE1040244B (en) |
| FR (1) | FR1182595A (en) |
| GB (1) | GB829601A (en) |
| LU (1) | LU35479A1 (en) |
| NL (2) | NL220985A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL99604C (en) * | 1955-03-23 | |||
| NL240880A (en) * | 1958-07-03 | |||
| DE1071339B (en) * | 1959-06-05 | 1959-12-17 | Deutsche Gold- und Silber Schei deanstalt vormals Roessler Frankfurt/M | Process for the production of polymers or copolymers of aerodynamics |
| US3118860A (en) * | 1959-11-09 | 1964-01-21 | Du Pont | Polymethacrolein derivatives |
| US3167529A (en) * | 1959-12-14 | 1965-01-26 | Shell Oil Co | Process for preparing high molecular weight polymers of unsaturated aldehydes and resulting products |
| DE1199979B (en) * | 1960-11-25 | 1965-09-02 | Dunlop Gummi Cie Ag Deutsche | Process for the production of cross-linked moldings from powdery polyacrolein |
| US3248355A (en) * | 1962-02-26 | 1966-04-26 | Union Carbide Corp | Solid polyacrolein-bisulfite adducts and process for the production thereof |
| US3322725A (en) * | 1962-08-07 | 1967-05-30 | Shell Oil Co | Process for preparing polymers having a high percent of free carbonyl and resulting products |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2212894A (en) * | 1937-11-08 | 1940-08-27 | Shell Dev | Polymerization of unsaturated aldehydes |
| US2485239A (en) * | 1945-03-06 | 1949-10-18 | Du Pont | Polymers containing recurring aldehyde groups and derivatives thereof and process for preparing same |
| US2569932A (en) * | 1945-11-21 | 1951-10-02 | Du Pont | Cross-linked hydrolyzed interpolymer of vinyl acetate and allylidene diacetate and process |
| US2657192A (en) * | 1951-01-25 | 1953-10-27 | Du Pont | Polymerization of acrolein |
-
0
- NL NL107667D patent/NL107667C/xx active
- NL NL220985D patent/NL220985A/xx unknown
- LU LU35479D patent/LU35479A1/xx unknown
- BE BE561137D patent/BE561137A/xx unknown
-
1956
- 1956-10-01 US US612926A patent/US2993878A/en not_active Expired - Lifetime
-
1957
- 1957-09-09 GB GB28440/57A patent/GB829601A/en not_active Expired
- 1957-09-11 FR FR1182595D patent/FR1182595A/en not_active Expired
- 1957-09-23 DE DEP19367A patent/DE1040244B/en active Pending
- 1957-09-27 CH CH5100657A patent/CH371596A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE561137A (en) | |
| CH371596A (en) | 1963-08-31 |
| FR1182595A (en) | 1959-06-26 |
| NL220985A (en) | |
| LU35479A1 (en) | |
| DE1040244B (en) | 1958-10-02 |
| US2993878A (en) | 1961-07-25 |
| NL107667C (en) |
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